Henry Winslow is the founder and editor of Tricycle Day, a twice-weekly newsletter that distills psychedelic research, policy, and culture into a 10-minute read.

In just two years, Henry’s grown an audience of over 65,000 subscribers by combining brute-force outreach, diversified revenue streams, and community building.

In This Episode, We Cover:

(05:39) Evolving Tricycle Day’s Business Model

(08:04) Growing Subscribers with Brute Force

(11:08) Newsletter Formats: Roundup vs. Q&A

(16:36) Turning Readers into a Community

(22:19) Upstream Marketing: From Problem to Solution

(28:06) Email Deliverability & Censorship Battles

(34:00) Customizing Your Community Platform

(39:22) Using Events to Build Your Brand

(45:01) The MDMA Therapy Approval Rollercoaster

Dan Barry’s Ad Sales as a Service helps media brands (especially newsletters) land more direct sponsorships and ad deals.

In this episode, Dan reveals the three biggest pitching mistakes and their simple fixes that will maximize your sponsorship ROI.

Chapters:

(00:00) Three Sponsorship Mistakes to Avoid

(05:33) Why Newsletter Sponsorships Stand Out

(10:53) Earning Sponsor Trust Quickly

(20:39) The Best Time to Monetize

(26:07) Essential Sales Skills for Sponsorship Pitches

(31:35) Boosting CPMs

(37:02) Low-Budget Marketing Hacks

(43:33) Crafting High-Conversion Lead Magnets

Nic Conley built his B2B sales newsletter, The Follow Up, to 7,000 subscribers in only 2 weeks. We sat down with Nic to break down exactly how he did it.

Chapters:

(02:04) Launching The Follow Up with the "Early Referral" Experiment

(07:42) Scaling with Paid Ads: Facebook & Twitter Tactics

(10:33) Owning Local Distribution

(21:22) Learning From Reader Replies

(30:00) Debriefing Virality vs Audience Fit

(35:00) Newsletter Advertising for Brand Marketing

(42:11) Content Lessons from the Wolf of Wall Street

Learn More About Orbit Marketing:

→ Visit Our Website: https://orbitmarketing.io/

→ Book A Call: https://api.leadconnectorhq.com/widget/booking/onkh0t7y3dIlC2Njpybl

→ Join Our Newsletter: https://newsletter.orbitmarketing.io/

Connect with Nic Conley:

→ Nic Conley's LinkedIn: https://www.linkedin.com/in/nicholasaconley/

→ Nic Conley's IG: https://www.instagram.com/itsnicconley/

→ Nic Conley's Twitter: https://x.com/niconley

→ Nic Conley's YouTube: https://www.youtube.com/channel/UCj88BHCCZgiBYNv4QryNEdQ

Read The Follow Up:

→ The Follow Up's LinkedIn: https://www.linkedin.com/company/the-follow-up/

→ The Follow Up's Website: https://www.jointhefollowup.com/subscribe